Chemical and Pharmaceutical Bulletin

Studies on Tertiary Amine Oxides. XV. Reaction of Quinoline 1-Oxide with Acetyl Cyanide.

Masatomo Hamana, Motoyoshi Yamazaki

1963 Volume 11 Issue 4 Pages 411-414
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.411

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While quinoline 1-oxide itself is not capable to react with acetyl cyanide, an exothermic reaction occurred in the presence of acetic anhydride, and quinaldonitrile and 2-quinolinepyruvonitrile were obtained. The former was a sole product from the reaction in dioxane or chloroform, whereas the latter was the main product without solvent.

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Studies on Tertiary Amine Oxides. XVI. Reactions of Quinoline 1-Oxides with Compounds Containing Reactive Hydrogens in the Presence of Acetic Anhydride.

Masatomo Hamana, Motoyoshi Yamazaki

1963 Volume 11 Issue 4 Pages 415-421
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.415

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Quinoline 1-oxides were found to react smoothly with compounds containing reactive hydrogens in the presence of acetic anhydride, producing the corresponding 2-substituted quinolines. The yields were generally good to excellent in the reactions of ethyl cyanoacetate, 1, 3-indandione, diethyl malonate, diethyl nitromalonate, ethyl nitroacetate (e. g. ethyl α-cyano-2-quinolineacetate in 88% yield), but acetone, acetophenone or phenylacetonitrile could not enter into the reaction. The reaction of quinoline 1-oxide using benzoyl chloride instead of acetic anhydride and those of pyridine 1-oxides in the presence of acetic anhydride proceeded similarly but in much lower yields.

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Metabolism of Drugs. XXXV. Metabolic Fate of Meprobamate. (3). A New Metabolic Pathway of Carbamate Group : The Formation of Meprobamate N-Glucuronide in Animal Body.

Hisao Tsukamoto, Hidetoshi Yoshimura, Kiyoshi Tatsumi

1963 Volume 11 Issue 4 Pages 421-426
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.421

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The structure of meprobamate-N-glucuronide, one of the principal metabolites of meprobamate, was established as meprobamate-N-mono-β-D-glucopyranosiduronic acid by direct condensation of meprobamate and glucuronic acid. It was also proved that this glucuronide was not formed spontaneously during the course of extraction but only by enzyme system in animal body.

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Metabolism of Drugs. XXXVI. The Metabolic Fate of Thiamylal[5-Allyl-5-(1-methylbutyl)-2-thiobarbituric Acid]. (2).

Hisao Tsukamoto, Hidetoshi Yoshimura, Hiroyuki Ide, Shoin Mitsui

1963 Volume 11 Issue 4 Pages 427-430
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.427

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Six among eight metabolites which were detected by paper chromatography, were isolated as crystalline compounds from the urine of rabbits administered thiamylal and all their structures were established as thiamylal ω-carboxylic acid, unchanged thiamylal, secobarbital, (ω-1)-hydroxythiamylal, secobarbital ω-carboxylic acid, and (ω-1)-hydroxysecobarbital, respectively. The fate of thiamylal ω-carboxylic acid, the main metabolite of thiamylal, was also studied and the possible in vivo metabolic map of thiamylal was speculated.

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thionamides. I. Synthesis. Demethylation of their N, N-Dimethyl Derivatives by Sulfur.

Tanezo Taguchi, Kunitoshi Yoshihira

1963 Volume 11 Issue 4 Pages 430-435
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.430

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Methylpyrazine (I) and 2-picoline (VI) were converted to N, N-dimethylpyrazinecar-bothionamide and N, N-dimethylpicolinethionamide (II and VII) respectively on fusion with sulfur in dimethylformamide. Iodine was found effective as a catalyst for the reaction. Besides the ordinal products (II and VII), the corresponding demethylated products were also isolated, thus indicating that the demethylation reaction, presumably due to the action of sulfur, was involved. The demethylation reaction was confirmed by the formation of N-methylpyrazinecarbothionamide and N-methylpicolinethionamide (III and VIII) from II and VII respectively on fusion with sulfur. II was 4 times more effective than pyrazinecarboamide against M. tuberculosis and its toxity was LD₅₀ 1180±15 mg./kg.

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Studies on Coenzyme Analogs. XIV. A New Phosphorylating Agent, Morpholinophosphorodichloridate.

Morio Ikehara, Eiko Ohtsuka

1963 Volume 11 Issue 4 Pages 435-440
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.435

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A new phosphorylating agent, morpholinophosphorodichloridate was synthesized from phosphorylchloride and morpholine. The reagent was used successfully for the synthesis of adenosine 5'-monophosphate and 6-dimethylamino-9-β-D-ribofuranosylpurine 5'-monophosphate. Starting from 2', 3'-di-O-acetyladenosine, adenosine 5'-di- and triphosphate were synthesized by phosphorylation with this reagent followed by the reaction with inorganic phosphate or pyrophosphate in fairy good overall yield.

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The Synthesis of 3-Spirooxindole Derivatives. I. Syntheses of 1-Methyl-2', 3', 10', 10'a-tetrahydrospiro [indoline-3, 1' (5'H)-pyrrolo [1, 2-b]-isoquinoline]-2-one and its Homologs.

Yoshio Ban, Takeshi Oishi

1963 Volume 11 Issue 4 Pages 441-445
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.441

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The syntheses of 1-methyl-2', 3', 10', 10'a-tetrahydrospiro [indoline-3, 1'(5'H)-pyrrolo-[1, 2-b]isoquinoline]-2-one (XIII) and its homologs were described. The compound XIII was identified with the dehydrogenation product of 1-methyl-2-hydroxy-3-[2-(1, 2, 3, 4-tetrahydro-2-isoquinolyl) ethyl] indole (XV), which established Belleau's assignment to the key intermediate in Julian's synthesis of the yohimbine ring system.

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The Synthesis of 3-Spirooxindole Derivatives. II. Syntheses of 1-Methylspiro-[indoline-3, 1'-pyrrolizidine and Indolizidine]-2-one.

Yoshio Ban, Takeshi Oishi

1963 Volume 11 Issue 4 Pages 446-451
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.446

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The syntheses of 1-methyl spiro[indoline-3, 1'-pyrrolizidine and -indolizidine]-2-one are described. The latter was obtained as two diastereoisomers, the stereochemistry of which was discussed mainly by their infrared absorption spectra.

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The Synthesis of 3-Spirooxindole Derivatives. III. Stereospecific Syntheses of rac-N-Methylrhynchophyllane for Stereochemistry of Rhynchophylline and Isorhynchophylline.

Yoshio Ban, Takeshi Oishi

1963 Volume 11 Issue 4 Pages 451-460
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.451

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N-Methylrhynchophyllane which is derived from the alkaloids, rhynchophylline and isorhynchophylline, was stereospecifically synthesized and was isolated as two pairs of stereoisomers, thereby establishing the trans-arrangement at C_6' and C_7' of these alkaloids.

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Synthesis of Methylpyridine Derivatives. XVI. The Reaction of Picolines and their N-Oxides with Amyl Nitrite.

Tetsuzo Kato, Yoshinobu Goto

1963 Volume 11 Issue 4 Pages 461-465
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.461

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The reactions of picolines and their N-oxides with amyl nitrite in the presence of metal amide or sodium hydroxide in liquid ammonia afforded the corresponding aldoximes and acid amides in comparatively good yields. It may be concluded that the methyl group of picoline is much less reactive than that of N-oxide and that the reactivity of methyl group in the pyridine ring increases in the order of 3-, 2-, and 4-position.

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Bromination of 2-Oxo Steroids

Tatsuhiko Nakano, Masahisa Hasegawa, Carl Djerassi

1963 Volume 11 Issue 4 Pages 465-472
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.465

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Bromination or enol acetylation of cholestan-2-one proceeds only towards C-3. Kinetically controlled bromination yields the axial 3α-bromo ketone, which can be equilibrated with hydrogen bromide to a ca. 1 : 1 mixture of 3α- and 3β-bromide. The latter is produced, together with cholest-3-en-2-one, upon treatment of 3α-bromocholestan-2-one with lithium cabonate and lithium bromide in dimethylformamide. 1α-Bromocholestan-2-one, synthesized independently from 1α, 2α-epoxycholestane, is not an intermediate in the formation of the 3α-bromo-2-ketone and is recovered unchanged after exposure to hydrogen bromide. The preparation of 2β-bromocholestan-1-one and its reaction with silver nitrate in acetic acid are also reported as are unsuccessful attempts to form the enol acetate of cholestan-1-one.

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Usnic Acid. IV. Isoanhydromethyldihydrousnic Acid.

Kotaro Takahashi, Shuichi Miyashita, Yoshie Ueda

1963 Volume 11 Issue 4 Pages 473-478
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.473

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The structure of isoanhydromethyldihydrousnic acid, one of the products by the acetylation of methyldihydrousnic acid has been shown as being (IIa). The reaction mechanism of the dehydration reaction has been discussed to show that it involes the fission and reformation of -C-O-C- linkage in the furan nucleus and successive Dienone-Phenol rearrangement. The difference in the mode of reaction at the intermediate dehydration process would result anhydromethyldihydrousnic acid (Ia) or iso-anhydromethyldihydrousnic acid (IIa).

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Studies on the Syntheses of Sucrose Fatty Acid Esters. I. Contents of Ester Parts in the Products of Alcoholyses.

Kazuya Kunugi

1963 Volume 11 Issue 4 Pages 478-482
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.478

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Alcoholyses of methyl stearate by sucrose were investigated, and the contents of Ester Parts produced under various molar ratios of sucrose/methyl stearate were determined. From the results obtained, in comparison with theoretical values, the composition of the alcoholysis product obtained by the reaction was assumed to be governed by the random distribution rule.

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Studies on the Syntheses of Sucrose Fatty Acid Esters. II. Separation of the Alcoholyses Products by Liquid Column Chromatography and Determination of the Contents of Sucrose Monostearate.

Kazuya Kunugi

1963 Volume 11 Issue 4 Pages 482-486
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.482

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Mixed sucrose stearates extracted from alcoholyses products at various molar ratios of sucrose/methyl stearate were separated by liquid column chromatography, and the contents of sucrose monostearate were determined. According to the comparison of the observed values with the theoretical ones, it was concluded that the composition of the alcoholysis product is governed by the random distribution rule, and it can be predicted by calculation with this rule. The compositions of various products were shown.

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Studies on the Syntheses of Sucrose Fatty Acid Esters. III. Re-esterification of Sucrose Monostearate.

Kazuya Kunugi

1963 Volume 11 Issue 4 Pages 486-489
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.486

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Re-esterification of sucrose monostearate at the condition similar to the alcoholysis reaction was investigated. Sucrose and sucrose polystearate, e. g., di- and tri-stearate, were produced as a result of re-esterification. It was concluded that the composition of the product gave a good accordance with the values calculated by the random distribution rule. Equilibrium was reached in about three hours.

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The Preparative and Pharmacological Studies of levo and dextro 9-Aza-des-N-morphinan (2, 3, 4, 4a-Tetrahydro-1H, 6H-5, 10b-propanophenanthridin-9-ol).

Goro Hayashi, Mikio Takeda, Hiroshi Kugita, Norio Sugimoto, Hajime Fuj ...

1963 Volume 11 Issue 4 Pages 489-494
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.489

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The analgesic effect was found in levo-isomer (DH-15) of 2, 3, 4, 4a-tetrahydro-1H, 6H-5, 10b-propanophenanthridin-9-ol, but not in dextro-isomer (DH-14). The analgesic effect of DH-15 was some what stronger than morphine, synergistic to morphine and antagonized by Levallorphane. The acute toxicity of DH-15 was far stronger than that of morphine. The pharmacological effects of DH-15 on the body temperature of mice and rats, barbiturate anaesthesia in mice, purpil of mice and gastrointestinal propulsion in mice were similar to that of morphine, but less active except barbiturate anaesthesia. DH-14 showed little effects. The contraction or increase of tonus in the isolated or in situ intestine of rabbits by the low dosis of DH-14 and DH-15 were observed.

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Syntheses and Antimicrobial Activity of 5-Alkyl-2-thiouracil Derivatives.

Sumiko Watanabe, Tadakazu Tsuji, Shigeshi Toyoshima

1963 Volume 11 Issue 4 Pages 495-499
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.495

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To find chemotherapeutic agents for polio, adenoviruses and toxoplasma Gondii, 2-thio-5-alkyl-6-aminouracil, 2-methylthio-5-alkyl-6-amino-4-pyrimidinol, 2-methylthio-4-chloro-5-alkyl-6-aminopyrimidine, 2-thio-5-alkyluracil and 2-thio-5-alkyl-6-methyluracil were synthesized. All of the compounds did not show any inhibitory effect on the viruses, but some of the compounds were found fairly effective against the infection of toxoplasma in mice. Death-delaying effect of 2-thio-5-hexyl-6-methyluracil, 2-methylthio-5-pentyl-6-amino-4-pyrimidinol and 2-methylthio-4-chloro-5-alkyl-6-aminopyrimidine which possess lower alkyl groups than hexyl group was found effective nearly equal to that of sulfadiazine or sulfamethazine.

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Bile Acids and Steroids. XXIII. Thiosteroids. (8). Intramolecular Condensation of Some 6-Acetylthio Steroids.

Kenichi Takeda, Taichiro Komeno, Shoichi Ishihara

1963 Volume 11 Issue 4 Pages 500-510
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.500

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The 3, 3-ethylenedioxy-5α, 6α-epoxy steroids were converted to the 5α-hydroxy-6β-acetylthio-3-oxo steroids by the action of thiolacetic acid. These were dehydrated, and following by epimerization of the substituent at position 6 converted to 6α-acetylthio-4-en-3-one steroids. The thiophene derivatives were obtained from the last mentioned compounds by the action of basic alumina.

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Preparation of Some Estriol Esters.

Kiyoshi Tsuneda, Joji Yamada, Kikuo Yasuda, Hiromu Mori

1963 Volume 11 Issue 4 Pages 510-514
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.510

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Estriol 16-monoacylates were obtained from estriol (I) by refluxing or warming estriol with carboxylic acids. A more drastic condition afforded estriol 16, 17-diacylates. Transesterification gave the same results. The reactions of estriol triacylates and estradiol diacylates with sodium borohydride gave estriol 16, 17-diacylates and estradiol 17-acylates, respectively. 3, 16α-Dihydroxyestra-1, 3, 5 (10)-trien-17-one diacetate (III) was transformed into estriol 16-acetate (IIa) by treatment with sodium borohydride. A milder condition afforded estriol 3, 16-diacetate (VI).

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The Reaction of N-Alkoxypyridinium Derivatives. (6). The Reaction of N-Methoxyquinolinium Salt with Ketones.

Toshihiko Okamoto, Hiroaki Takayama

1963 Volume 11 Issue 4 Pages 514-517
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.514

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N-Alkoxyquinolinium salts were reacted with several ketones and corresponding quinaldyl ketones were obtained as the reaction products. This reaction was accompanied by partial decomposition of the quaternary salt into the tertiary base and aldehyde.

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Researches on Chemotherapeutic Drugs Against Viruses. XXXV. Syntheses and Antiviral Activity of Alkylated Ephedrine and its Related Compounds.

Mitsuru Furukawa, Shigeshi Toyoshima

1963 Volume 11 Issue 4 Pages 518-523
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.518

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In order to find antiviral compound, alkyl group was introduced into the neurotropic structure of ephedrine and activity of the resulting alkyl derivatives were examined against the Nakayama strain of Japanese B encephalitis virus, Type-1 Mahoney strain of polio virus and Type-1 strain of adeno virus. Among these derivatives, [2-(3, 4-dimethylphenyl)-2-hydroxyisopropyl] trimethylammonium iodide and 1-(2-methoxy-5-methylphenyl)-2-aminopropanol showed in vitro effect, and only the former exerted in vivo activity on the Nakayama strain.

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Studies on Acetylenic Compounds. XXX. Absolute Configuration of 1, 4-Diphenyl-2-butyn-1, 4-diol.

Issei Iwai, Kazuo Tomita

1963 Volume 11 Issue 4 Pages 524-528
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.524

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1 (R), 4 (R)-(-)-1, 4-Diphenyl-2-butyn-1, 4-diol (IIIb) was obtained accompanying with the meso-diol (IIIa) by Grignard reaction of (R)-(-)-1-phenyl-2-propyn-1-ol and benzaldehyde. Each of diasteroisomers was oxidized with manganese dioxide to the same 1, 4-diphenyl-2-butyn-1, 4-dione. The levorotatory glycol (IIIb) was derived to the corresponding diacetate V, which was oxidized with aqueous potassium permanganate into O-acetyl-(S)-(+)-mandelic acid (VI) and the absolute configuration of IIIb was further confirmed as (R) -system. 1 (S), 4 (S)-(+)-1, 4-Diphenyl-2-butyn-1, 4-diol (IIIc) was similarly obtained from (S)-(+)-1-phenyl-2-propyn-1-ol and benzaldehyde. A stoichiometric mixture of the enantiomorphs (IIIb and IIIc) gave the racemic compound IV melted at 101∼102°.

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Untersuchungen uber Steroide. XXIX. Versuche zur Synthese von Cholesta-7, 22-dien-3β-ol.

Kiyoshi Sakai, Kyosuke Tsuda

1963 Volume 11 Issue 4 Pages 529-530
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.529

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Es wird Cholesta-7, 22-dien-3β-ol aus 3β-Acetoxy-20β-methylpregn-7-en-21-carboxaldehyd durch Wittig-Reaktion erhalten.

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Studies on the Synthesis of Munjistin. II. Synthesis of 3-O-Methyldamnacanthal.

Yoshio Hirose, Haruko Ueno, Motoko Iwashita, Eiko Kawagishi

1963 Volume 11 Issue 4 Pages 531-532
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.531

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Synthesis of 3-O-methyldamnacanthal (VI), m. p. 185∼186°, was described.

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Studies on the Synthesis of Munjistin. III. Syntheses of 2-Hydroxymethylpurpurin and its Derivatives.

Yoshio Hirose

1963 Volume 11 Issue 4 Pages 533-534
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.533

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Syntheses of 3-purpurinmethanol and its derivatives were reported.

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The Structure of Evodol, a Principle of Evodia rutaecarpa.

Yoshio Hirose

1963 Volume 11 Issue 4 Pages 535-536
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.535

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Steroid Series. XI. Synthesis of B-Norsteroid.

Katsumi Tanabe, Yasuhiro Morisawa

1963 Volume 11 Issue 4 Pages 536-538
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.536

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Cholesterol acetate (Ia), 3β-hydroxypregn-5-en-20-one acetate (Ib) and 3β-hydroxyandrost-5-en-17-one acetate (Ic) were ozonized in dichloromethane containing a small amount of methanol to give the corresponding 3β-acetoxy-5-hydroxy-6-methoxy-5, 6-peroxy-5, 6-seco steroid compounds (IIa, b, c), which on reduction with zinc dust and acetic acid afforded 3β-acetoxy-5-oxo-5, 6-secosteroid-6-als (IIIa, b, c). Cyclization reaction of (IIIa, b, c) was conducted by stirring with alumina in benzene solution to yield 6β-formyl-B-nor-5β-cholestane-3β, 5-diol 3-acetate (IVa), 6β-formyl-3β, 5-dihydroxy-B-nor-5β-pregnan-20-one 3-acetate (IVb) and 6β-formyl-3β, 5-dihydroxy-B-nor-5β-androstan-17-one 3-acetate (IVc), respectively.

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Synthesis of Quinoline Derivatives of Amino Acid.

Toshio Kakimoto, Kyozo Hayashi, Tomoji Suzuki

1963 Volume 11 Issue 4 Pages 538-540
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.538

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To investigate competition growth inhibition of heterocyclic amino acids, five compounds of 3-(8-quinolyl) alanine, 3-(3-bromo-8-quinolyl) alanine, 3-(5-nitro-8-quinolyl) alanine, 3-(2-quinolyl) alanine and α-amino-2-quinolinebutyric acid were synthesized by the method of amino acid synthesis with ethyl acetamidocyanoacetate.

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Studies on Benzoisogranatanine Derivatives. II. Synthesis of 1-Phenethyl-2, 4-propano-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolines.

Toyonari Oine, Hiroshi Kugita, Mikio Takeda

1963 Volume 11 Issue 4 Pages 541-543
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.541

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1-Phenethyl-2, 4-propano-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolines (B), a structure related to A has been synthesized by lithium aluminum hydride reduction of VI followed by the bromination to VII (R=Br), and dehydrobromination with diluted alkaline solution.

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Biosynthesis of Sinigrin

Mitsuyoshi Matsuo, Mikio Yamazaki

1963 Volume 11 Issue 4 Pages 545-547
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.545

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Structure of Kessane

Hiroshi Hikino, Yasuko Hikino, Yasuyoshi Takeshita, Kazuko Shirata, Ts ...

1963 Volume 11 Issue 4 Pages 547-548
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.547

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Isolation of (-) S-Propenyl-L-cysteine from Garlic

Michiyasu Sugii, Tomoji Suzuki, Shigeharu Nagasawa

1963 Volume 11 Issue 4 Pages 548-549
Published: April 25, 1963
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.11.548

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